Nickel-catalyzed diastereoselective alkyl-alkyl Kumada coupling

A nickel pincer complex is found to catalyze alkyl–alkyl Kumada coupling reactions of 1,3- and 1,4-substituted cyclohexyl halides and tetrahydropyrans with an excellent diastereoselectivity. The mechanistic investigation of the coupling reactions provides evidence that the activation of alkyl halides is reversible.